6,9a-dihydroxy-6,9-dimethyl-3-methylidene-4,5,6a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-2,7-dione

Details

• Internal ID: 0e8c677e-5270-4e21-8025-0904f8c7ec08
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives
• IUPAC Name: 6,9a-dihydroxy-6,9-dimethyl-3-methylidene-4,5,6a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-2,7-dione
• SMILES (Canonical): CC1=CC(=O)C2C1(C3C(CCC2(C)O)C(=C)C(=O)O3)O
• SMILES (Isomeric): CC1=CC(=O)C2C1(C3C(CCC2(C)O)C(=C)C(=O)O3)O
• InChI: InChI=1S/C15H18O5/c1-7-6-10(16)11-14(3,18)5-4-9-8(2)13(17)20-12(9)15(7,11)19/h6,9,11-12,18-19H,2,4-5H2,1,3H3
• InChI Key: VXENIKHPXCFDEG-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₈O₅
• Molecular Weight: 278.30 g/mol
• Exact Mass: 278.11542367 g/mol
• Topological Polar Surface Area (TPSA): 83.80 Ų
• XlogP: -0.40
• Atomic LogP (AlogP): 0.51
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 0

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9351	93.51%
Caco-2	-	0.5242	52.42%
Blood Brain Barrier	+	0.5277	52.77%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.5179	51.79%
OATP2B1 inhibitior	-	0.8562	85.62%
OATP1B1 inhibitior	+	0.8503	85.03%
OATP1B3 inhibitior	+	0.9410	94.10%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7342	73.42%
BSEP inhibitior	-	0.9726	97.26%
P-glycoprotein inhibitior	-	0.9036	90.36%
P-glycoprotein substrate	-	0.7572	75.72%
CYP3A4 substrate	+	0.6346	63.46%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9043	90.43%
CYP3A4 inhibition	-	0.7818	78.18%
CYP2C9 inhibition	-	0.8151	81.51%
CYP2C19 inhibition	-	0.8368	83.68%
CYP2D6 inhibition	-	0.9138	91.38%
CYP1A2 inhibition	-	0.6880	68.80%
CYP2C8 inhibition	-	0.7601	76.01%
CYP inhibitory promiscuity	-	0.9459	94.59%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5495	54.95%
Eye corrosion	-	0.9789	97.89%
Eye irritation	-	0.8796	87.96%
Skin irritation	-	0.5349	53.49%
Skin corrosion	-	0.8039	80.39%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5673	56.73%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	+	0.6533	65.33%
skin sensitisation	-	0.7824	78.24%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.8333	83.33%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.3168	31.68%
Estrogen receptor binding	+	0.7072	70.72%
Androgen receptor binding	+	0.6901	69.01%
Thyroid receptor binding	+	0.5216	52.16%
Glucocorticoid receptor binding	-	0.4922	49.22%
Aromatase binding	-	0.6193	61.93%
PPAR gamma	+	0.5249	52.49%
Honey bee toxicity	-	0.9072	90.72%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9229	92.29%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.30%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.85%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.54%	97.25%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.08%	99.23%
CHEMBL2581	P07339	Cathepsin D	86.38%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.06%	100.00%
CHEMBL1907600	Q00535	Cyclin-dependent kinase 5/CDK5 activator 1	83.72%	93.03%
CHEMBL241	Q14432	Phosphodiesterase 3A	83.35%	92.94%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.23%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.20%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.97%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.46%	86.33%

Plants that contains it

• Artemisia rutifolia
• Artemisia xanthochroa
• Schistostephium umbellatum

Cross-Links

• PubChem: 14414265
• LOTUS: LTS0022824
• wikiData: Q105298456